Ammonium Chloride → 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzamide

HRID 1877520Notes

Reaction equation

HRID 1877520 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=N1.OC1C2N=N[NH:34]C=2C=CC=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C.C(C1N=CC([C:57]2[C:69]3[C:68]4[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=4)[N:62]([C:70]4[CH:78]=[CH:77][C:73]([C:74](O)=[O:75])=[C:72]([NH:79][CH2:80][CH2:81][F:82])[CH:71]=4)[C:61]=3[CH:60]=[CH:59][CH:58]=2)=CC=1)#N>CN(C)C=O.O>[C:11]([C:16]1[N:8]=[CH:12][C:13]([C:57]2[C:69]3[C:68]4[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=4)[N:62]([C:70]4[CH:78]=[CH:77][C:73]([C:74]([NH2:34])=[O:75])=[C:72]([NH:79][CH2:80][CH2:81][F:82])[CH:71]=4)[C:61]=3[CH:60]=[CH:59][CH:58]=2)=[CH:14][CH:15]=1)#[N:10]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 866551674-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 583382204-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

58 mg of (1H-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (BOP), 18 mg of hydroxybenzotriazole (HOBT), 9 mg of ammonium chloride and 0.07 ml of diisopropylethylamine are successively added to a solution of 40 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzoic acid in 30 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 2 hours and then diluted with distilled water and extracted with ethyl acetate. The organic phase is subsequently washed with distilled water and a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane, acetonitrile and methanol (96/2/2 by volume), so as to gve 30 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(2-fluoroethyl)amino]benzamide in the form of a white solid, the characteristics of which are the following:

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is subsequently washed with distilled water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution
  7. additionbeing carried out with a mixture of dichloromethane, acetonitrile and methanol (96/2/2 by volume)

Sources & evidence

ORD record
ord-6666bf634ebc4846ba5c14c865ab2de3
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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